Styrene oxide

Chemical properties

colourless to light yellow liquid

Chemical properties

Styrene oxide is a colorless to pale strawcolored liquid. Pleasant, sweet odor.

The Uses of Styrene oxide

A major (toxic) metabolite of Styrene (S687790), catalyzed by epoxide hydrolase.

The Uses of Styrene oxide

Styrene oxide is is an important intermediate for organic synthesis and is widely used in organic synthesis, pharmaceutical preparation, and perfume production. For example, styrene oxide is added to hydrogen to produce monophenylethanol under the action of a catalyst.
Styrene oxide has a wide range of uses, and can be used in floral fragrances for daily use, as well as in food. Styrene oxide is also an important intermediate for the synthesis of levamisole hydrochloride. L-imidazole hydrochloride is a broad-spectrum intestinal repellent that can be used by humans and animals.

The Uses of Styrene oxide

Used as an intermediate in the production of styrene glycol and its derivatives; as a reactive dilutent in the epoxy resin industry; as a chemical intermediate for making bphenethyl alcohol, a fragrance material.

Definition

ChEBI: An epoxide of styrene.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 6668, 1984 DOI: 10.1021/ja00334a035
Tetrahedron Letters, 21, p. 4449, 1980 DOI: 10.1016/S0040-4039(00)92196-8

General Description

Clear colorless straw-colored liquid with a sweet pleasant odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Styrene oxide is incompatible with oxidizing agents. Also incompatible with acids and bases. Reacts with 4-(4'-nitrobenzyl)pyridine. Polymerizes exothermally and reacts vigorously with compounds possessing a labile hydrogen (e.g. alcohols and amines) in the presence of catalysts such as acids, bases and certain salts .

Hazard

Toxic by ingestion and inhalation. Possible carcinogen.

Health Hazard

Styrene oxide is a mild to moderate skin irri-tant. Irritation from 500 mg was moderateon rabbit skin. The toxicity of this com-pound was low on test animals. Inhalationof 500 ppm in 4 hours was lethal to rats. Anin vivo and in vitro study in mice (Helmanet al. 1986) indicates acute dermal toxicity,causing sublethal cell injury.
LD50 value, oral (mice): 1500 mg/kg
Styrene oxide, however, may present aconsiderable health hazard as a mutagen,teratogen, and carcinogen. The reproduc-tive effects from inhalation observed in ratswere fetotoxicity, developmental abnormal-ities, and effects on fertility (Sikov et al.1986). There is sufficient evidence of its car-cinogenicity in animals, producing liver, gas-trointestinal tract, and skin tumors. Gavageexposure caused cancer in the forestomach ofboth sexes of rats and mice (McConnell andSwenberg 1994). Its cancer-causing effectson humans are unknown.
No exposure limit has been set for thiscompound. Its toxic and irritant effects inhumans are quite low.

Fire Hazard

Styrene oxide is combustible.

Flammability and Explosibility

Non flammable

Potential Exposure

Styrene oxide is used as a reactive intermediate, especially to produce styrene glycol and its derivatives. Substantial amounts are also used in the epoxy resin industry as a diluent. It may also have applications in the preparation of agricultural and biological chemicals, cosmetics, and surface coatings and in the treatment of textiles and fibers. Styrene oxide is made in quantities in excess of a million pounds per year, and further, is a presumed metabolite of styrene which is produced in much greater quantities.

Carcinogenicity

Styrene-7,8-oxide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Fractional distillation under reduced pressure does not remove phenylacetaldehyde. If this material is present, the styrene oxide is treated with hydrogen under 3 atmospheres pressure in the presence of platinum oxide. The aldehyde, but not the oxide, is reduced to .-phenylethanol, and separation is now readily achieved by fractional distillation. [Schenck & Kaizermen J Am Chem Soc 75 1636 1953, Beilstein 17/1 V 577.]

Incompatibilities

Vapors may form explosive mixture with air. May polymerize on heating above 200C, under the influence of strong acids, strong bases; oxidizers, metal salts; such as aluminum chloride; catalysts for vinyl polymers. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Styrene oxide is burned in a chemical incin-erator equipped with an afterburner andscrubber.